Reaktionsgleichung
[O:1]=[C:2]1[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:37](Br)[CH:38]=[CH2:39].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:39]([C@H:3]1[C:2](=[O:1])[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:4]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:38]=[CH2:37]Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
10 g of tert-butyl (5S,6R)-2-oxo-5,6-diphenylmorpholine-4-carboxylate were dissolved in 200 ml of THF and cooled to −78° C. 63 ml of a 0.5 M solution of KHMDS in toluene were added dropwise and, after stirring for 10 min, 3.7 ml of allyl bromide were added dropwise. The mixture was allowed to warm from −78° C. to −20° C. over the course of 3 h, and the reaction was then stopped by adding 300 ml of a saturated ammonium chloride solution. 200 ml of ethyl acetate were added, and the phases were separated. The aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was stirred with diisopropyl ether.
Aufarbeitung
- temperatureto warm from −78° C. to −20° C. over the course of 3 h
- customthe phases were separated
- extractionThe aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time
- dry with materialthe combined organic phases were dried with MgSO4
- customThe solvents were removed in vacuo
- stirringthe residue was stirred with diisopropyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-9f364c30dc6f4b19af11cf7bacabaeaa
- Quelldatensatz
- uspto-grants-2006_03
- Patentnummer
- US07008957B2
Verknüpfte Notizen
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